Fluoro-containing ether monomer for fabricating contact lenses, contact lenses materials and contact lenses obtained therefrom

ABSTRACT

The invention provides a fluoro-containing ether monomer for fabricating contact lenses represented by following formula (I): 
                         
In formula (I), R 10  is fluoroalkyl group (C x F y H z , wherein x is an integer of 2-20, y is an integer of 5-30, and y+z=2x+1), R 11  is oxygen, nitrogen or sulfur; R 12  is C 1 -C 3  alkylene; n is an integer of 3-40.

CROSS-REFERENCE TO RELATED APPLICATION

The present application is a Divisional application of the applicationSer. No. 13/917,656 filed Jun. 14, 2013, the entire contents of whichare hereby incorporated herein by reference.

BACKGROUND

1. Technical Field

The present invention relates to a composition for fabricating contactlenses. More particularly, the composition for fabricating contactlenses comprising a fluoro-containing ether monomer.

2. Description of Related Art

In the early years hard contact lenses were mainly made of glass. Thesoft contact lenses were therefore developed to improve the discomfortof wearing of the hard contact lenses. The soft contact lenses can beclassified into two categories, hydrogel contact lenses and siliconehydrogel contact lenses.

The hydrogel contact lenses are made from hydrogel materials, such aspoly-2-hydroxyethyl methacrylate (p-HEMA). Since the water content ofthe p-HEMA is only about 38.8%, one or more than one kinds of thehydrophilic monomer, for example N-vinylpyrrolidone (NVP),N,N-dimethylacrylamide (DMA) and methyl acrylic acid (MAA), are added toenhance the water content of such materials for the contact lenses.

With the addition of the hydrophilic monomer, the water content of thecontact lenses can increase up to 80%. However, the higher water contentof the contact lens is, the lower tension and toughness thereof become.Therefore, the water content of contact lenses is generally controlledin the range from about 45% to 58% to have a sufficient mechanicalstrength for the contact lenses.

For improving the disadvantages of the hydrogel contact lenses, siliconecontact lenses with excellent oxygen permeability (DK) have been studiedfor a number of years. The silicone hydrogel contact lenses are made bypolymerizing a hydrophilic silicone polymeric material and a hydrophilicmonomer.

However, the lipid secreted from the human eyes would produce lipiddeposition on the contact lenses and result in discomfort when wearing.It is known in the prior art that the fluorosilicone acrylate issuitable for manufacturing contact lenses because of having high oxygenpermeability, which can reduce corneal disease from hypoxia. Inaddition, the contact lenses also provide comfort of wearing and not toabsorb ocular secretions. But the disadvantage of the contact lenses ispoor in flexibility.

Thus, the present invention provides a novel fluoro-containing ethermonomer for fabricating contact lenses and the contact lensesfabricating therefrom have desirable physical properties and iscomfortable in wearing.

SUMMARY

Proteins in the tears are easily absorbed on the surface of the contactlenses, which may induce lipid deposition thereon. The present inventionprovides a fluoro-containing ether monomer for fabricating contactlenses which can prevent such lipid deposition, provide the comfort ofwearing and have better oxygen permeability (DK).

According to an aspect of the present invention, the fluoro-containingether monomer for fabricating contact lenses is provided. Thefluoro-containing ether monomer is represented by the following formula(I):

wherein R₁₀ is fluoroalkyl group (C_(x)F_(y)H_(z), wherein x is aninteger of 2 to 20, y is an integer of 5 to 30, and y+z=2x+1); R₁₁ isoxygen, nitrogen or sulfur; R₁₂ is C₁-C₃ alkylene group and n is aninteger of 3 to 40.

The present fluoro-containing ether monomer for fabricating contactlenses can be used in hydrogel contact lenses and in silicone hydrogelcontact lenses. Thus, a composition for fabricating contact lenses isprovided. According to an aspect of the present invention, thecomposition for fabricating contact lenses comprises: afluoro-containing ether monomer represented by the following formula(I):

wherein R₁₀ is fluoroalkyl group (C_(x)F_(y)H_(z), wherein x is aninteger of 2 to 20, y is an integer of 5 to 30, and y+z=2x+1); R₁₁ is aoxygen, nitrogen or sulfur; R₁₂ is C₁-C₃ alkylene group; and n is aninteger of 3 to 40; at least one hydrophilic monomer; at least onesiloxane macromer and an initiator.

According to another aspect of the present invention, the compositionfor fabricating contact lenses comprises a fluoro-containing ethermonomer represented by the above formula (I); at least one hydrophilicmonomer and an initiator.

The above and other aspects of the invention will become betterunderstood with regard to the following detailed description of thepreferred but non-limiting embodiment(s).

DETAILED DESCRIPTION

In the following detailed description, for purposes of explanation,numerous specific details are set forth in order to provide a thoroughunderstanding of the disclosed embodiments. It will be apparent,however, that one or more embodiments may be practiced without thesespecific details.

The present invention provides a composition for fabricating contactlenses that can prevent from lipid deposition, provide better oxygenpermeability and adequate water content.

According to an aspect of the present invention, a fluoro-containingether monomer for fabricating contact lenses is provided. Thefluoro-containing ether monomer is represented by the following formula(I):

wherein, R₁₀ is fluoroalkyl group (C_(x)F_(y)H_(z), wherein x is aninteger of 2 to 20, y is an integer of 5 to 30, and y+z=2x+1); R₁₁ is aoxygen, nitrogen or sulfur; R₁₂ is C₁-C₃ alkylene group and n is aninteger of 3 to 40.

In an embodiment of the present invention, the molar ratio of fluorineto carbon in fluoro-containing ether monomer is in the range of 0.032 to0.88. Moreover, the fluoro-containing ether monomer is present at anamount of 0.07 to 0.4 weight percent based on the total amount of thecontact lenses.

In an embodiment of the present invention, the fluoro-containing ethermonomer is represented by the following formula (I-1), wherein R₁₀ isC₅F₅H₆; R₁₁ is oxygen, R₁₂ is CH₂CH₂ and n is n is an integer of 3 to40.

In an embodiment of the present invention, the fluoro-containing ethermonomer is represented by the following formula (I-2), wherein R₁₀ isC₁₀F₁₇H₄, R₁₁ is oxygen, R₁₂ is CH₂CH₂ and n is n is an integer of 3 to40.

In an embodiment of the present invention, the fluoro-containing ethermonomer is represented by the following formula (I-3), wherein R₁₀ isC₁₀F₁₇H₄, R₁₁ is sulfur, R₁₂ is CH₂CH₂ and n is n is an integer of 3 to40.

According to an aspect of the present invention, a composition forfabricating contact lenses comprises a fluoro-containing ether monomerrepresented by the formula (I); at least one siloxane macromer; at leastone hydrophilic monomer and an initiator.

In an embodiment of the present invention, the siloxane macromercomprises a first siloxane macromer and a second siloxane macromer, Thefirst siloxane macromer is represented by the following formula (II) ora siloxane macromer represented by the following formula (III):

wherein in formula (II), p is an integer of 4 to 80,

wherein in formula (III), q is an integer of 4 to 80 and r is an integerof 3 to 40. The second siloxane macromer represented by the followingformula (IV), with the number average molecular weight of 1,000 to10,000 and the second siloxane macromer has cross-linking functionalgroups;

wherein R₁, R₂ and R₃ are independently C₁-C₄ alkyl groups, R₄ is C₁-C₆alkenylene group, C₁-C₆ alkylene group, or C₁-C₆ alkylene substitutedwith ether group, R₅ is O or NH, R₆ is C₁-C₆ alkylene group or C₁-C₆alkylene substituted with ether group, R₇ is H, C₁-C₆ alkylene group orC₁-C₆ alkylene substituted with ether group, R₈ is a residue of reactivefunctional group with hydroxyl group, carboxyl group, epoxy group oracid anhydride group, and n is a integer of 10 to 100.

In an embodiment of the present invention, the second siloxane macromercan be represented by the following formula (IV-1):

wherein in formula (IV-1), the s is an integer of 10 to 100.

In an embodiment of the present invention, the hydrophilic monomer canbe but not limited to, N-vinylpyrrolidone (NVP), 2-hydroxyethylmethacrylate (HEMA), N,N-dimethylacrylamide (DMA), methyl acrylic acid(MAA), acrylic acid, glycidyl methacrylate (GMA), (methyl)acrylamide,2-(N,N-dimethylamino) ethyl methacrylate (DMAEMA), vinyl acetate,2-(Dimethylamino)ethyl methacrylate, N-acrylolmorpholine and acombination thereof.

Besides, the initiator suitably used in conventional for manufacturingcontact lenses can be used in the composition of the present invention,can be a thermal initiator or a photoinitiator. The suitable thermalinitiator, can be not limited to, such as, for example,azobisisoheptonitrile, 2,2′-azobis(isobutyronitrile) (AIBN),2,2′-azobis(2,4-dimethylvaleronitrile),2,2′-azobis(2-methyl-propanenitrile),2,2′-azobis(2-methyl-butanenitrile). The suitable photoinitiator, can benot limited to, such as, for example, 2-Hydroxy-2-methylpropiophenone,1-Hydroxycyclohexyl phenyl ketone, 2,2-Dimethoxy-2-phenylacetophenone,Benzoin methyl ether, 2,2′-azobis-isobutyronitrile or2,2-Diethoxyacetophenone.

In the composition for fabricating contact lenses aforementioned, thefirst siloxane macromer is present at an amount of 30 to 60 parts byweight, the second siloxane macromer is present at an amount of 1 to 15parts by weight, the hydrophilic monomer is present at an amount of 30to 65 parts by weight, the fluoro-containing ether monomer is present atan amount of 0.1 to 0.3 parts by weight and the initiator is present atan amount of 0.1 to 1 parts by weight based on the total amount of thecomposition.

In an embodiment of the present invention, the composition forfabricating contact lenses further includes a crosslinking agent,UV-blocking agent, dye, a UV-blocking agent and a combination of.Moreover, the crosslinking agent suitably used in conventionalcompositions for manufacturing contact lenses can be used in the methodof the present invention, such as, for example, ethylene glycoldimethacrylate (EGDMA), tetraethylene ethylene glycol dimethacrylate(TEGDMA), tetraethylene ethylene glycol dimethacrylate (TrEGDMA),Poly(ethylene glycol) dimethacrylate, trimethylolpropane trimethacrylate(TMPTA), vinyl methacrylate, ethylenediamine dimethyl acrylamide,glycerol dimethacrylate, triallyisoeyanurate or triallyl cyanurate.

According to an aspect of the present invention, a composition forfabricating contact lenses comprises a fluoro-containing ether monomerrepresented by the formula (I-1); a first siloxane macromer representedby the formula (II) and a second siloxane macromer represented by theformula (IV-1):

wherein in formula (I-1), n is an integer of 3 to 40.

In the embodiment of the invention, the hydrophilic monomer is acombination of HEMA and NVP or a combination of a NVP, HEMA and DMA.According to an aspect of the present invention, a composition forfabricating contact lenses comprises a fluoro-containing ether monomerrepresented by the formula (I-1), a first siloxane macromer representedby the formula (III) and a second siloxane macromer represented by theformula (IV-1). In the embodiment of the invention, the hydrophilicmonomer is a combination of a NVP, HEMA and DMA.

According to an aspect of the present invention, a composition forfabricating contact lenses comprises a fluoro-containing ether monomerrepresented by the formula (I-2); a first siloxane macromer representedby the formula (II) and a second siloxane macromer represented by theformula (IV-1):

wherein in formula (I-2), n is an integer of 3 to 40.

In the embodiment of the invention, the hydrophilic monomer is acombination of DMA, HEMA and NVP, a combination of HEMA and DMA, or acombination of NVP and HEMA.

In an embodiment of the invention, a composition for fabricating contactlenses comprises a fluoro-containing ether monomer represented by theformula (I-2); a first siloxane macromer represented by the formula(III) and a second siloxane macromer represented by the formula (IV-1).In the embodiment of the invention, the hydrophilic monomer is acombination of HEMA and DMA.

In an embodiment of the invention, a composition for fabricating contactlenses comprises a fluoro-containing ether monomer represented by theformula (I-3); a first siloxane macromer represented by the formula (II)and a second siloxane macromer represented by the formula (IV-1):

wherein in formula (I-3), n is an integer of 3 to 40.

In the embodiment of the invention, the hydrophilic monomer is acombination of HEMA and NVP.

In an embodiment of the invention, a composition for fabricating contactlenses comprises a fluoro-containing ether monomer represented by theformula (I-3); a first siloxane macromer represented by the formula(III) and a second siloxane macromer represented by the formula (IV-1).In the embodiment of the invention, the hydrophilic monomer is acombination of HEMA and DMA.

According to another aspect of the present invention, a composition forfabricating contact lenses comprises a fluoro-containing ether monomeraforementioned; at least one hydrophilic monomer aforementioned; aninitiator aforementioned and a crosslinking agent aforementioned. In theembodiment of the invention, the hydrophilic monomer is a combination ofNVP, HEMA and MAA.

In the composition for fabricating contact lenses, the hydrophilicmonomer is present at an amount of 100 parts by weight, thefluoro-containing ether monomer is present at an amount of 0.1 to 0.3parts by weight, the crosslinking agent is present at an amount of 0.5to 1.0 parts by weight, and the initiator is present at an amount of 0.1to 1 parts by weight based on the total amount of the composition.

According to a further another aspect of the present invention, a methodfor fabricating contact lenses is provided. The present method cancomprise but not limited to the following steps (a) to (b):

In step (a), a first siloxane macromer, a second siloxane macromer, atleast one hydrophilic monomer, fluoro-containing ether monomer and aninitiator are mixed to form a mixture. To simplify the description, thefirst siloxane macromer, the second siloxane macromer, the hydrophilicmonomer, the fluoro-containing ether monomer and the initiator mentionedabove didn't describe in detail.

In the mixture, the first siloxane macromer is present at an amount of30 to 60 parts by weight, the second siloxane macromer of is present atan amount of 1 to 15 parts by weight, the hydrophilic monomer is presentat an amount of 30 to 65 parts by weight, the fluoro-containing ethermonomer is present at an amount of 0.1 to 0.3 parts by weight, and theinitiator is present at an amount of 0.1 to 1 parts by weight based onthe total amount of the mixture.

In addition, the mixture further includes solvent, a crosslinking agent,a dye, a UV-blocking agent and a combination of. The solvent is forexample, such as ethanol or hexanol.

In step (b), the mixture is injected into a mold of contact lens andconducted a UV irradiating treatment or a thermal treatment to formcontact lenses.

The thermal treatment is conducted at temperature in the range betweenabout 60° C. to about 120° C., and the reaction time is in the rangefrom about 1 hour to 12 hours. In an embodiment of the method of thepresent invention, the thermal treatment is conducted at 80° C. for 10hours.

After forming contact lenses, the method of the present inventionfurther comprises a hydration treatment. In an embodiment of the methodof the present invention, the hydration treatment comprises but notlimited to the following steps.

Firstly, the contact lenses are soaked solvent, for example, isopropylalcohol or ethanol, then soaked in water, and finally soaked in a buffersolution to reach equilibrium. The buffer solution is, for example, abuffered saline.

According to a further another aspect of the present invention, contactlenses obtained by the method mentioned above is provided.

From the physical property test, the oxygen permeability (DK) of thecontact lenses according to the present invention is more than 90, andpreferably more than 150. By comparison with contact lenses withfluoro-containing ether monomer free, the contact lenses made offluoro-containing ether monomer can actually enhance oxygen permeability(DK) of contact lenses.

Moreover, the water content of the contact lenses according to thepresent invention is more than 30%. In another embodiment of the presentinvention, the water content of the contact lenses is in the range about30% to 55%.

The present invention will be explained in further detail with referenceto the examples. However, the present invention is not limited to theseexamples.

EXAMPLE

The Preparation of First Siloxane Macromer (A1)

The siloxane macromer (A1), commercial code, MCR-M11 (the number averagemolecular weight is about 1000), is obtained from Gelest.

The Preparation of First Siloxane Macromer (A2)

4.44 g of isophorone diisocyanate, 0.0025 g of dibutyltin dilaurate asthe catalyst, and 40 mL of methylene chloride were added to a flask, andthe solution was stirred under a stream of nitrogen. Then, 20 g ofmonocarbinol terminated polydimethylsiloxane (commercial code, MCR-C12,the number average molecular weight is about 1000, from Gelest) wasaccurately weighed and added dropwise to the solution over about 1 hour.After the solution reacting at room temperature for 12 hours, another0.0025 g of dibutyltin dilaurate and 7.2 g of polyethylene glycolmonomethacrylate (the number average molecular weight is about 526) wereaccurately weighed and added dropwise to the solution over about 1 hour.After the solution reacting at room temperature for another 12 hours,the resulting reaction product was washed with a large amount of water,and then dehydrated and filtered to obtain a raw product. Then, themethylene chloride was evaporated to obtain a siloxane macromer (A2)(the number average molecular weight is about 1700).

The Preparation of Second Siloxane Macromer (B)

20 g (0.02 mole) of aminopropyl terminated polydimethylsiloxane(commercial code DMS-A12, the number average molecular weight is about1000, from Gelest), 4.5 g of itaconic anhydride (0.040 mole) and 40 mLof methylene chloride were added to a flask to form a solution, then thesolution was stirred at room temperature. After the solution stirring atroom temperature for 12 hours, the resulting reaction product was washedwith a large amount of water, and then dehydrated and filtered to obtaina raw product. Then, the methylene chloride was evaporated to obtain asiloxane macromer (B) (the number average molecular weight is about1200).

The Properties of Siloxane Macromer (B)

NMR Spectroscopy:

The results of analysis of ¹H-NMR exhibited as follows:

-   1H-NMR (400 MHz, CDCl₃), δ 6.36 (s, 1H), 5.82 (s, 1H), 3.39-3.21 (m,    4H), 1.62-1.42 (m, 2H), 062-0.47 (m, 2H), 0.19-0.02 (Si—CH₃).    IR Spectroscopy:-   (1) Absorption bands derived from Si—CH₃ at 802 cm⁻¹ and 1259 cm⁻¹.-   (2) Absorption bands derived from Si—O—Si at 1032 cm⁻¹ and 1100    cm⁻¹.

The Preparation of Fluoro-Containing Ether Monomer (I-1)

12 g of isophorone diisocyanate, 0.0012 g of dibutyltin dilaurate as thecatalyst, and 40 mL of methylene chloride were added to a flask, and thesolution was stirred under a stream of nitrogen. Then, 10 g of4,4,5,5,5-Pentafluoro-1-pentanol was accurately weighed and addeddropwise to the solution over about 20 mins. After the reaction at roomtemperature for 6 hours, another 0.0012 g of dibutyltin dilaurate and 20g polyethylene glycol monomethacrylate (the number average molecularweight is about 360) were accurately weighed and added dropwise to thesolution over about 20 mins. After the solution stirring for 12 hours,the resulting reaction product was washed with a large amount of water,and then dehydrated and filtered to obtain a raw product. Then, themethylene chloride was evaporated to obtain a fluoro-containing ethermonomer (I-1) (the number average molecular weight is about 745).

The Preparation of Fluoro-Containing Ether Monomer (I-2)

12 g of isophorone diisocyanate, 0.0012 g of dibutyltin dilaurate as thecatalyst, and 40 mL of methylene chloride were added to a flask, and thesolution was stirred under a stream of nitrogen. Then, 25 g of1H,1H,2H,2H-Perfluoro-1-decanol was accurately weighed and addeddropwise to the solution over about 20 mins. After the solution reactingat room temperature for 6 hours, another 0.0012 g of dibutyltindilaurate and 20 g polyethylene glycol monomethacrylate (the numberaverage molecular weight is about 360) were accurately weighed and addeddropwise to the solution over about 20 mins. After the solution stirringfor 12 hours, the resulting reaction product was washed with a largeamount of water, and then dehydrated and filtered to obtain a rawproduct. Then, the methylene chloride was evaporated to obtain afluoro-containing ether monomer (I-2) (the number average molecularweight is about 1046).

The Preparation of Fluoro-Containing Ether Monomer (I-3)

12 g of isophorone diisocyanate and 40 mL of methylene chloride wereadded to a flask and the solution was stirred under a stream ofnitrogen. Then, 26 g of 1H,1H,2H,2H-perfluorodecanethiol was accuratelyweighed and added dropwise to the solution over about 20 mins. Thereaction temperature is controlled at 60° C. for 6 hours. Then, theflask is cooled down to room temperature and another 0.0012 g ofdibutyltin dilaurate and 20 g polyethylene glycol monomethacrylate (thenumber average molecular weight is about 360) were accurately weighedand added dropwise to the solution over about 12 hrs. The resultingreaction product was washed with a large amount of water, and thendehydrated and filtered to obtain a raw product. Then, the methylenechloride was evaporated to obtain a fluoro-containing ether monomer(I-3) (the number average molecular weight is about 1060).

The Properties of Fluoro-Containing Ether Monomer (I-3)

NMR Spectroscopy

(1) A peak of methyl protons derived from isophorone diisocyanate ataround from 0.7 ppm to 1.1 ppm.

(2) A peak of methyl protons of methacryloy group at around 1.88 ppm.

(3) A peak of vinyl protons of methacryloy group at around 5.54 ppm and6.09 ppm.

(4) A peak derived from CH₂—F at around from 1.60 ppm to 1.71 ppm, 2.20ppm to 2.04 ppm, 3.71 ppm to 3.65 ppm.

IR Spectroscopy

(1) Absorption bands derived from Si—CH₃ at 802 cm⁻¹ and 1259 cm⁻¹.

(2) Absorption bands derived from Si—O—Si at 1032 cm⁻¹ and 1100 cm⁻¹.

(3) Absorption bands derived from C═O of methacryloy group at 1720 cm⁻¹.

The Preparation of the Contact Lenses

The Preparation of the Contact Lenses of Example 1

A siloxane macromer (A1), a siloxane macromer (B), N-vinylpyrrodine(NVP), 2-hydroxyethyl methacrylate (HEMA), N,N-dimethylacrylamide (DMA),fluoro-containing ether monomer (I-1), a thermal initiator,2-2′-azobis(isobutyronitrile) (AIBN) and hexanol were mixed at theamounts shown in Table 1 and stirred about 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthereof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

The Preparation of the Contact Lenses of Example 2

A siloxane macromer (A1), a siloxane macromer (B), N-vinylpyrrodine(NVP), 2-hydroxyethyl methacrylate (HEMA), a thermal initiator,2-2′-azobis(isobutyronitrile) (AIBN), fluoro-containing ether monomer(I-1) and hexanol were mixed at the amounts shown in Table 1 and stirredabout 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthereof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

The Preparation of the Contact Lenses of Example 3

A siloxane macromer (A2), a siloxane macromer (B), N-vinylpyrrodine(NVP), 2-hydroxyethyl methacrylate (HEMA), N,N-dimethylacrylamide (DMA),a thermal initiator, 2-2′-azobis(isobutyronitrile) (AIBN),fluoro-containing ether monomer (I-1) and ethanol were mixed at theamounts shown in Table 1 and stirred about 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthereof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

The Preparation of the Contact Lenses of Example 4

A siloxane macromer (A1), a siloxane macromer (B), N-vinylpyrrodine(NVP), 2-hydroxyethyl methacrylate (HEMA), N,N-dimethylacrylamide (DMA),a thermal initiator, 2-2′-azobis(isobutyronitrile) (AIBN),fluoro-containing ether monomer (I-2) and ethanol were mixed at theamounts shown in Table 1 and stirred about 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthereof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

The Preparation of the Contact Lenses of Example 5

A siloxane macromer (A2), a siloxane macromer (B),N,N-dimethylacrylamide (DMA), 2-hydroxyethyl methacrylate (HEMA), athermal initiator, 2-2′-azobis(isobutyronitrile) (AIBN),fluoro-containing ether monomer (I-2) and ethanol were mixed at theamounts shown in Table 1 and stirred about 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthereof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

The Preparation of the Contact Lenses of Example 6

A siloxane macromer (A1), a siloxane macromer (B), 2-hydroxyethylmethacrylate (HEMA), N,N-dimethylacrylamide (DMA), a thermal initiator,2-2′-azobis(isobutyronitrile) (AIBN), fluoro-containing ether monomer(I-2) and ethanol were mixed at the amounts shown in Table 1 and stirredabout 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthereof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

The Preparation of the Contact Lenses of Example 7

A siloxane macromer (A1), a siloxane macromer (B), N-vinylpyrrodine(NVP), 2-hydroxyethyl methacrylate (HEMA), a thermal initiator,2-2′-azobis(isobutyronitrile) (AIBN), fluoro-containing ether monomer(I-3) and ethanol were mixed at the amounts shown in Table 1 and stirredabout 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthereof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

The Preparation of the Contact Lenses of Example 8

A siloxane macromer (A1), a siloxane macromer (B), N-vinylpyrrodine(NVP), 2-hydroxyethyl methacrylate (HEMA), a thermal initiator,2-2′-azobis(isobutyronitrile) (AIBN), fluoro-containing ether monomer(I-3) and ethanol were mixed at the amounts shown in Table 1 and stirredabout 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthereof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

The Preparation of the Contact Lenses of Example 9

A siloxane macromer (A2), a siloxane macromer (B), 2-hydroxyethylmethacrylate (HEMA), N,N-dimethylacrylamide (DMA), a thermal initiator,2-2′-azobis(isobutyronitrile) (AIBN), fluoro-containing ether monomer(I-3) and ethanol were mixed at the amounts shown in Table 1 and stirredabout 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthereof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

The Preparation of the Contact Lenses of Example 10

A siloxane macromer (A1), a siloxane macromer (B), 2-hydroxyethylmethacrylate (HEMA), N-vinylpyrrodine (NVP), a thermal initiator,2-2′-azobis(isobutyronitrile) (AIBN), fluoro-containing ether monomer(I-1) and ethanol were mixed at the amounts shown in Table 1 and stirredabout 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthereof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

The Preparation of the Contact Lenses of Example 11

A siloxane macromer (A1), a siloxane macromer (B), N-vinylpyrrodine(NVP), 2-hydroxyethyl methacrylate (HEMA), a thermal initiator,2-2′-azobis(isobutyronitrile) (AIBN), fluoro-containing ether monomer(I-2) and ethanol were mixed at the amounts shown in Table 1 and stirredabout 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthereof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

The Preparation of the Contact Lenses of Example 12

A siloxane macromer (A1), a siloxane macromer (B), N-vinylpyrrodine(NVP), 2-hydroxyethyl methacrylate (HEMA), a thermal initiator,2-2′-azobis(isobutyronitrile) (AIBN), fluoro-containing ether monomer(I-3) and ethanol were mixed at the amounts shown in Table 1 and stirredabout 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthereof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

The Preparation of the Contact Lenses of Comparative Example 1

A siloxane macromer (A1), a siloxane macromer (B), N-vinylpyrrodine(NVP), 2-hydroxyethyl methacrylate (HEMA), N,N-dimethylacrylamide (DMA),a thermal initiator, 2-2′-azobis(isobutyronitrile) (AIBN), and hexanolwere mixed at the amounts shown in Table 1 and stirred about 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthererof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

The Preparation of the Contact Lenses of Comparative Example 2

A siloxane macromer (A1), a siloxane macromer (B), N-vinylpyrrodine(NVP), 2-hydroxyethyl methacrylate (HEMA), a thermal initiator,2-2′-azobis(isobutyronitrile) (AIBN), and hexanol were mixed at theamounts shown in Table 1 and stirred about 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthereof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

The Preparation of the Contact Lenses of Comparative Example 3

A siloxane macromer (A2), a siloxane macromer (B), N-vinylpyrrodine(NVP), 2-hydroxyethyl methacrylate (HEMA), N,N-dimethylacrylamide (DMA),a thermal initiator, 2-2′-azobis(isobutyronitrile) (AIBN), and ethanolwere mixed at the amounts shown in Table 1 and stirred about 1 hour.

Then, the mixtures were injected into a mold of contact lens made ofpolypropylene(PP) and heated to initiate the radical polymerizationthereof at 80° C. for 10 hrs.

After the polymerization was completed, the mold was immersed inisopropyl alcohol solution for 1 hour and the resulting molded lens wastaken out of the mold. The resulting lens was immersed in heated waterfor 4 hrs and then immersed in a buffer solution to reach equilibrium.

Physical Property Tests

The results of physical property tests of Comparative Example1-Comparative Example 3, and Example 1-Example 12 of the presentinvention were shown as the following Table 2.

As shown in Table 2, Examples 1 to Example 12 of the present inventionhave more excellent oxygen permeability than Comparative Example 1 toComparative Example 3 with fluoro-containing ether monomer free. Inaddition, the water content of Example 1 to Example 12 are about 33% to54%, the modulus of Example 1 to Example 12 are about 0.35 MPa to 0.65MPa, the tension of Example 1 to Example 12 are about 15 g to 83 g, theoxygen permeability (DK) of Example 1 to Example 12 are about 93 to 166.

While the invention has been described by way of example(s) and in termsof the preferred embodiment(s), it is to be understood that theinvention is not limited thereto. On the contrary, it is intended tocover various modifications and similar arrangements and procedures, andthe scope of the appended claims therefore should be accorded thebroadest interpretation so as to encompass all such modifications andsimilar arrangements and procedures.

TABLE 1 The composition of contact lenses of Example 1 - Example 12 andComparative Example 1-3 Comparative Example Compo- Example (wt %)Example (wt %) sition Function Abbr. 1 2 3 1 2 3 4 5 6 7 8 9 10 11 12First Siloxane A1 34.5 41.8 34.5 41.8 44.4 50.1 35.4 38.8 38 38 38siloxane macromer macromer (A1) Siloxane A2 47.5 47.5 38.6 38.6 macromer(A2) Second Siloxane B  7.1  6.3  7.1  7.1  6.3  7.1  5.8  5.8  5.5  7.2 7.3  5.8 10.2 10.2 10.2 siloxane macromer macromer (B) HydrophilicN-vinyl- NVP 47.2 44.9 28.6 47.2 44.9 28.5 18.1 47.3 48.5 36.7 36.7 36.7monomer pyrrodine 2-hydroxy- HEMA  6.5  6.3  8.3  6.5  6.3  8.3 13.513.5 13.5  9.5  4.8 13.5 14.5 14.5 14.5 ethyl meth- acrylate N,N- DMA 4.7  8.3  4.7  8.3 17.9 41.5 30.3 41.5 dimethyl acrylamide fluoro-fluoro- I-1  0.1  0.2  0.2  0.2 containing containing ether ethermonomer monomer (I-1) fluoro- I-2  0.3  0.2  0.2  0.2 containing ethermonomer (I-2) fluoro- I-3  0.2  0.2  0.3  0.2 containing ether monomer(I-3) thermal 2-2-azobis AIBN  0.7  0.7  0.7  0.7  0.7  0.7  0.6  0.6 0.6  0.6  0.6  0.6  0.6  0.6  0.6 initiator (isobutyro- nitrile)Solvent Hexanol HeOH 25 25 25 25 Ethanol EtOH 25 25 10 10 20 25 25 10 2020 20

TABLE 2 The physical properties of contact lenses of Example 1-12 andComparative Example 1-3 Comparative Example Example Item 1 2 3 1 2 3 4 56 7 8 9 10 11 12 Water content 34.8 55.5 55.5 34.9  40.2  41.8  43.353.1  41.6  34.4  51.5  50 4  44.5  41.5  42.2 (%) Modulus (Mpa)  0.63 0.39  0.34  0.39  0.42  0.38  0.65  0.42  0.64  0.63  0.58  0.39  0.590.65 0 65 Tension (g) 16.6 16.2 17.1 15  21  19  60 53  83  17  37  55 41  38  40 Oxygen 81 88 89 94 150 155 157 93 166 103 101 110 142 157155 permeability (Dk)

What is claimed is:
 1. A composition for fabricating contact lensescomprising: a fluoro-containing ether monomer represented by thefollowing formula (I):

wherein in formula (I), R₁₀ is fluoroalkyl group C_(x)F_(y)H_(z),wherein x is an integer of 2 to 20, y is an integer of 5 to 30, andy+z=2x+1; R₁₁ is a oxygen, nitrogen or sulfur; R₁₂ is C₁-C₃ alkylenegroup; and n is an integer of 3 to 40; at least one hydrophilic monomer;at least one siloxane macromer; and an initiator.
 2. The composition forfabricating contact lenses according to claim 1, wherein the siloxanemacromer comprising: a first siloxane macromer represented by thefollowing formula (II) or a siloxane macromer represented by thefollowing formula (III):

wherein in formula (II), p is an integer of 4 to 80; and

in formula (III), q is an integer of 4 to 80 and r is an integer of 3 to40, a second siloxane macromer, represented by the following formula(IV), having the number average molecular weight in a range of 1,000 to10,000 and the second siloxane macromer with cross-linking functionalgroups,

wherein R₁, R₂ and R₃ are independently C₁-C₄ alkyl groups, R₄ is C₁-C₆alkenylene group, C₁-C₆ alkylene group, or C₁-C₆ alkylene substitutedwith ether group, R₅ is O or NH, R₆ is C₁-C₆ alkylene group or C₁-C₆alkylene substituted with ether functional group, R₇ is H, C₁-C₆alkylene group or C₁-C₆ alkylene substituted with ether group, R₈ is aresidue of reactive functional group with hydroxyl group, carboxylgroup, epoxy group or acid anhydride group, and n is a integer of 10 to100.
 3. The composition for fabricating contact lenses according toclaim 2, wherein the first siloxane macromer is present at an amount of30 to 60 parts by weight, the second siloxane macromer of is present atan amount of 1 to 15 parts by weight, the hydrophilic monomer is presentat an amount of 30 to 65 parts by weight, the hydrophilicfluorine-containing ether monomer is present at an amount of 0.1 to 0.3parts by weight, and the initiator is present at an amount of 0.1 to 1parts by weight based on the total amount of the composition.
 4. Acomposition for fabricating contact lenses according to claim 1, whereinthe hydrophilic monomer is selected from the group consisting ofN-vinylpyrrolidone (NVP), 2-hydroxyethyl methacrylate (HEMA),N,N-dimethylacrylamide (DMA), methyl acrylic acid, acrylic acid,glycidyl methacrylate (GMA), (methyl)acrylamide, 2-(N,N-dimethylamino)ethyl methacrylate (DMAEMA), vinyl acetate, 2-(dimethylamino)ethylmethacrylate, N-acrylolmorpholine and a combination thereof.
 5. Acomposition for fabricating contact lenses according to claim 1, whereinin formula (I), R₁₀ is C₅F₅H₆ or C₁₀F₁₇H₄; R₁₁ is oxygen or sulfur andR₁₂ is CH₂CH₂.